MobFellas: Simels, Gleeson, and Shargel

The only-in-NY trial that brings together a lawyer to drug kingpins, his mob attorney, and the Gotti prosecutor

Legendary local attorney Robert Simels is only being punished for representing some of New York's most unredeemable gangsters, say some in local legal circles. Kind of a what-goes-around-comes-around situation.

Simels not only lawyered for mafia turncoat Henry Hill (on whose life GoodFellas was based), but also some of the biggest Latino and black drug kingpins of the '80s and '90s. And now, Simels himself is in deep trouble. He's been indicted for allegedly tampering with witnesses in a case revolving around a comparatively little-known Guyanese drug gangster, Shaheed "Roger" Khan.

As it happens, the veteran lawyer is also the star of a reunion that could only happen in New York City. Simels is being tried before U.S. Judge John Gleeson, who made his rep as a dogged prosecutor of John Gotti. And for his own defense, Simels has hired Gerald Shargel, one of Gotti's main lawyers and a guy who is, in fact, one of the most prominent mob lawyers in the city.

While some people may see this as an attempt to deliver a comeuppance to Bob Simels, you won't see him showing up in Gleeson's court as a meek supplicant. Nor will you see the prosecutors doing any pussyfooting. "That is basically the underlying story here," says Nicholas Pileggi, author of Wiseguy, the book on Henry Hill that was adapted for Martin Scorsese's GoodFellas. "Simels takes great joy in being a criminal defense lawyer. He goes in there with his smirk and his expensive clothes and likes to piss off guys who make $80,000 a year."

Pileggi, who worked with Simels on both the book and the movie deal, adds: "The government hasn't forgotten about the past, and they want to rap him on the knuckles. These are not the kind of people who leave the game at the ballpark."

It's somewhat strange that Khan is overshadowed in all this. Though he's not particularly well-known to the general public here, he's a South American drug kingpin. But to New Yorkers, Khan is likely to stay in the background. Here's one of those rare cases in which the gangster reaches a plea agreement with prosecutors, and the gangster's lawyer winds up facing trial.

A DEA agent's affidavit—based mostly on audiotapes of Simels allegedly tampering with witnesses in the Khan case—was enough to bring the obstruction charges against Khan, Simels, and a Simels associate, Arienne Irving.

During his preparation for his defense of Khan, the government says, Simels and Irving discussed a slew of ways to obstruct justice and otherwise tamper with witnesses, "from offering them money to murdering their family members." The government claims to have recorded conversations during which Simels allegedly talked about "neutralizing" witnesses—and not in a benign way.

When Simels, Khan, and Irving were indicted last September, Simels had to recuse himself from Khan's defense team. Last month, Khan accepted a plea deal, admitting to cocaine trafficking as well as to the witness-tampering charges stemming from the Simels tapes, in exchange for an expected 15-year sentence. (The deal allowed Khan to avoid being nailed on charges of operating a "continuing criminal enterprise.") Lawyers for both Khan and Simels swear that the plea deal had nothing to do with Simels's arrest or Shargel's involvement in defending him, although, as part of his deal, Khan (who has not been formally sentenced) will not have to testify against his former attorney.

As for Simels? He's free on $3.5 million bail and could face up to 10 years in prison, which, for the 62-year-old high-flying lawyer, could mean an end to his career.


By any accounting, Robert Simels stepped into a hornets' nest in Guyana when he took on the case of Roger Khan, who was arrested in 2006 by DEA agents in Suriname, Guyana's eastern neighbor, and renditioned to New York via Trinidad. Simels was hired, family members and associates say, on the strength of his reputation for taking high-profile drug cases.

Khan, 37, besides being an alleged drug lord, is also accused of having been the driving force behind the "Phantom Squad," a shadowy, extrajudicial police force linked to some 200 killings in Guyana. From at least 2001 until his arrest, the DEA says, "Khan . . . obtained large quantities of cocaine, and then imported the cocaine into the Eastern District of New York and other places, where it was further distributed. Khan was ultimately able to control the cocaine industry in Guyana, in large part, because he was backed by a paramilitary squad that would murder, threaten, and intimidate others at Khan's direction. Khan's enforcers committed violent acts and murders on Khan's orders that were directly in furtherance of Khan's drug trafficking conspiracy."

Khan's story is not that of a simple drug runner, though. In 1993, while he was living in Vermont and already had one felony under his belt, he was indicted for possession of a firearm, released on $1,000 bail, and "departed to his native country of Guyana and never returned to the United States," according to a court document prepared by John Bergendahl, another of his attorneys. In Guyana, "Khan founded and operated a number of successful businesses, including, but not limited to, a housing development and a construction company, a carpet cleaning service, a nightclub, and a timber mill."

Khan's reputation seems to diverge along racial lines in Guyana, where about half the population is of African descent and half of East Indian descent, like him. To many Indo-Guyanese, he is a folk hero, responsible for cleaning up the streets when the country's police force—which is predominantly Afro-Guyanese—couldn't or wouldn't, giving East Indians, who dominate the business community, a layer of protection where none previously existed. Khan has claimed, without copping to the existence of the Phantoms, to have helped the government put down a crime spree stemming from a 2002 prison break, and to have collaborated with the U.S. government in the region, most notably in the case of the safe retrieval of an American diplomat who was kidnapped off a Guyana golf course in 2003. Afro-Guyanese are more likely to associate Khan first and foremost as a leader of the Phantom Squad—a drug runner and thug, to blame for just about every suspicious death in Guyana. (Guyana, like Suriname, is a transshipping point for South American cocaine destined for North America, Europe, West Africa, and the Caribbean, according to the DEA.)

"Certainly, the numerous, unexplained deaths that we had in Guyana have not been there" since Khan has been off the streets, says Raphael Trotman, a Guyanese lawyer and founder of the Alliance for Change, a political party that aims to be non-racialized. Trotman says that while he has no direct evidence of Khan's involvement in the Phantoms, things have been noticeably calmer in Guyana since his arrest. "There is a correlation between the lack of deaths and his absence." (Vic Puran, Khan's Guyana-based lawyer, calls the Phantoms—and Khan's involvement in them—just that: a figment of the imagination.)

After Khan's arrest, Simels made two trips to Guyana, where the case has dominated the press, to organize his defense. On one of these trips, in July 2007, he held a press conference at which he seemed to play to Guyana's racial politics in order to argue that Khan was the victim of a politically motivated frame-up. Simels then proceeded to list the names of presumptive witnesses against Khan—even going so far as to spell out their names—and discredit them through linking them to involvement in the drug trade.

In a small country like Guyana—with its population of about 800,000, most located in or around the capital of Georgetown—the naming of witnesses was widely interpreted as putting them at risk of retribution from the Phantoms or from emboldened enemies of the incarcerated Khan.

None of the names blared out by Simels, however, had been listed by the prosecution as witnesses. Dora Irizarry, the presiding judge in the Khan case, granted a government motion to have a gag order placed on Simels. Irizarry wrote that Simels's statements at the press conference "appear to serve no purpose other than to attempt to silence, intimidate, and harass the identified individuals and to put them and their families and friends, many of whom live in Guyana or within Guyanese communities in the United States, in danger." She added that "he practically provided the press with a road map to some of their homes, spelling out names and identifying the family business in Guyana of one named individual." The lawyer's comments, she wrote, "ran so obviously contrary to his obvious ethical duties that, at one point, even members of the press . . . questioned the propriety of Simels's remarks."

It wasn't only the press that was questioning Simels's propriety—and it wasn't only Simels's public remarks that were being scrutinized. Without his knowledge, the attorney was being monitored by government investigators. According to DEA agent Cassandra Jackson's affidavit, Simels told an informant that if the informant was called to testify, he (or she) "would need to lie about certain things," and that a certain witness, "John Doe No. 1"—the same witness Simels supposedly expressed interest in "neutralizing"—was the linchpin of the government's case. Simels allegedly told the informant that he or she could help Khan by locating "possible government witnesses and/or the witnesses' family members" so that they might help influence potential witnesses' testimonies.

In a subsequent meeting, according to the affidavit, Simels reiterated that he wanted John Doe No. 1 not to testify, saying that "we need to know every little detail of his life" and that "the government's case will collapse if the witness is neutralized by us [pause] or neutralized by us on cross-examination." The affidavit goes on to say, somewhat cryptically, that "Simels further explained that they should explore both options."

"I think [John Doe No. 1] might rethink his position once we start reaching out to his extensions," the informant allegedly said to Simels, continuing, "One thing I've learned is that a man—whether he's a criminal, he's a preacher, he always values his mother. . . . You don't ever want anything to happen to her."

According to the affidavit, Simels then cautioned the informant about killing the witness's mother, but said, "Whatever [Khan's] got to do financially, he's going to do to resolve these issues. [Pause.] There is money that's available." Then the informant, according to the affidavit, "suggested that John Doe No. 1 'might suddenly get amnesia,' " to which Simels allegedly replied, "That's a terrible thing, but if it happens, it happens."

The informant, according to the court documents, "asked Simels about the possibility of 'heat' coming back to Khan if a government witness stops cooperating and refuses to testify because someone close to him or her 'fall[s] off the face of the earth.' Simels replied: 'They'd have to figure out a way to tie it back to Roger [Khan]. . . . But [pause] it seems to me that—that [pause] I'm going to leave it to you to figure out what's going to best get to [John Doe No. 1].' "

Later in the summer, in another meeting at Simels's office, according to the affidavit, the informant told Simels that another witness, "Jane Doe No. 2," was "willing to testify in conformity with Khan's defense." Simels then allegedly typed up a statement outlining what he wanted the witness to say, including that John Doe No. 1 was affiliated with a terrorist organization and that he intended to falsely testify against Khan. According to the affidavit, "the document also had blank spaces in which Jane Doe No. 2 was to add names. The informant then told Simels that Jane Doe No. 2 wanted $10,000 in exchange for signing the document."

In a subsequent telephone conversation about the payment, which was recorded by the informant, Simels allegedly said, "Tell her that obviously she can't get any money until she meets with me, but that I'll make the agreement with her. . . . She's got to meet with me. If she does it and she signs the document, she gets half then and she gets half when she, ah, finishes testifying."

The taped conversations make up the meat of agent Jackson's affidavit, which has landed Simels in trouble and has now brought together in one courtroom three of the most notable figures in the recent history of New York mobsters and the lawmen who pursued them.


Gerald Shargel and John Gleeson first clashed during one of John Gotti's trials in the early '90s. Shargel, who had been for some time an attorney for members of the Gambino crime family, was part of the Gotti defense team, which also included Bruce Cutler, a barrel-chested, bombastic defense attorney who, through his combative courtroom manner, played the role of bad cop to Shargel's good cop. It was Gleeson, then a prosecutor, who engineered the disqualification of Shargel and Cutler from Gotti's defense, on the grounds that they had become "house counsel" to the Gambino crime family. Gleeson's argument stemmed from recorded conversations at the Ravenite Social Club (now a shoe store on Mulberry Street), in which John Gotti is heard complaining about the high price tag that accompanied Shargel and Cutler.

Gleeson threatened for years to bring Shargel and Cutler up on charges of witness tampering and obstruction of justice, based on the Ravenite tapes and possible testimony from Sammy "the Bull" Gravano, Gotti's underboss and a former Shargel client, who began cooperating with the government in 1991. After a four-year investigation, the U.S. Attorney's office abandoned pursuing charges against Shargel and Cutler.

Gleeson, who became a judge in 1994, has a glowing reputation in legal and law enforcement circles. Bruce Mouw, the former Gambino case supervisor for the FBI, says Gleeson was "one of the finest prosecutors I've ever worked with, a quality professional."

Perhaps the strongest testimonial to Gleeson's reputation as a mob-busting prosecutor came in 1992, when Gotti's new lawyers sought to have Gleeson removed from the Gotti case because he had an "intense personal interest" in prosecuting the crime boss.

While Gleeson was making his reputation and then ascending to the federal bench, Shargel has become one of the most sought-after criminal defense attorneys in the city, having represented a rogue's gallery of accused mobsters—including Jimmy Burke, the model for Robert De Niro's Jimmy Conway character in GoodFellas—and a host of other high-profile clients, including Stanley Friedman, the former Bronx borough president convicted of racketeering in 1986. Shargel is now working on the defense of the accused money launderer Marc Dreier, another prominent New York attorney.

Even his opponents attest to Shargel's competence. Sean Haran—a former prosecutor who faced off against Shargel in the money-laundering case involving the rap label Murder, Inc.—recalls that Shargel virtually put on a clinic: "He is extremely well prepared, knows the evidence, exploits every weakness," Haran says. "The guy knows what he's doing."

And Shargel has tried a case before Gleeson, one not without similarities to the Simels case. In the murder trial of Michael Burnett—a lifelong con man who was the driving force behind the graft scandal at the New York City Parking Violations Bureau that ensnared Friedman—Shargel defended attorney Howard Krantz, who was accused of supplying a hired killer with a gun used to kill a Staten Island bank teller who was set to testify against Burnett in a fraud trial. In the trial, Shargel categorized his client as a dupe, but Krantz was convicted.

Shargel is smooth enough, of course, to say he's pleased that Gleeson is the trial judge on Simels's case. "I have enormous respect for him," Shargel says. "As a taxpayer, you get what you pay for with him. He's a fair and intelligent judge."

As for Simels? "He is willing to do things that lawyers shouldn't do on behalf of their clients," says a former prosecutor and adversary of Simels who declines to be named. "Some attorneys go beyond being advocates and become part of the organization, which is unfortunate because Simels is a competent lawyer, but he definitely crosses the line. I've seen enough of Bob Simels that it does not surprise me that his name has come up as someone who would be in this kind of trouble."

Not so, says Shargel.

Concerning the affidavit and other contentions by prosecutors, Shargel calls the conversations on the tapes "a cat and mouse game," in which ambiguous conversations "dangle in mid-air" and, besides, contain material that is "profoundly helpful" to his defense of Simels.

Shargel won't directly touch the topic of whether the prosecution of Simels's conduct is punitive, saying only, "I have my own private thoughts on the motive for sending in a . . . wired cooperator on very scant evidence of anything."


The allegations contained in the government's indictment of Bob Simels are similar to allegations that have dogged him for years, particularly those levied against him during the 1988 trial of accused drug kingpin Brooks Davis.

During that trial, court documents show, Simels paid a visit to a witness, who had confessed to the government his involvement in the attempted murder of a witness against Davis. When Davis and the cooperating witness were mistakenly put into the same holding cell in the Metropolitan Correctional Center, Davis allegedly told the witness that he would send his lawyer, Simels, to see him. According to court documents, "the purpose of the lawyer's visit was for [the witness] to sign a paper stating that he 'ain't going to testify.' "

Two days later, Simels presented an affidavit from the informant that said his previous statements to the government about Davis were false. The government then presented evidence stating that, during his visit with the informant at MCC, Simels warned the informant that "he should not testify against his 'friends' from the 'street,' while [his] family [was] out there." A mistrial was declared as the specter of Simels's becoming a witness in the trial loomed.

You almost have to think that Bob Simels would know better than to get himself in this kind of trouble. He began his career in the early '70s in the New York State Special Prosecutor's Office, where he worked on the prosecution of corruption cases involving links between the NYPD and organized crime.

Simels has told Pileggi that, upon entering private practice in the late '70s, he had always wanted to be a mob lawyer, but because of his association with Hill, who was considered a "rat," Italian gangsters sought to distance themselves from him. Simels wound up representing drug kingpins who have become street legends, such as "Boy George" Rivera, who, by the time he was arrested at 21, according to the feds, had amassed some $15 million from his "Obsession" brand of heroin. (In 1991, Rivera received a life sentence without parole.) Another of Simels's clients, Thomas "Tony Montana" Mickens, was known for his profligate spending, acumen as a money launderer, and obsessive admiration for Al Pacino's Scarface character. He is now serving a 35-year sentence.

Another of Simels's clients was Lorenzo "Fat Cat" Nichols, the Jamaica, Queens, drug gang leader now serving a life sentence on narcotics charges and an additional 40-year sentence for the 1985 murder of his parole officer. It was Nichols's associate, Howard "Pappy" Mason, who was convicted in the murder of rookie police officer Edward Byrne, a killing that brought a new level of law enforcement scrutiny and public attention to the kingpins, and signaled the beginning of the end of their reign.

Of Simels's kingpin clients, perhaps none is more notorious than Kenneth "Supreme" McGriff, who, along with his violent "Supreme Team" drug gang, turned South Jamaica Queens' Baisley housing projects into what is said to be one of the models for the Carter, the enormous crackhouse/storehouse in the movie New Jack City. McGriff's stature in southeast Queens—along with romanticized notions about his influence there—have made him a point of reference for many rappers. (Indeed, it was 50 Cent's detailed description of the Supreme Team organization's machinations in his song "Ghetto Qu'ran" that, prevailing street wisdom has it, led to his being shot nine times during a 2000 attempt on his life.) In 1989, under Simels's counsel, McGriff pleaded guilty to drug charges and served the better part of eight years behind bars (he had been facing 150 years). In 2005, he was charged, along with Irv and Chris Gotti, née Lorenzo, with laundering Supreme Team drug money through the rap label Murder, Inc., which was headed by Irv Lorenzo. Their case was ultimately separated from that of McGriff, and the Lorenzos, with Gerald Shargel as part of their defense team, were eventually acquitted. McGriff was charged with ordering the murder of two rivals in 2001 and is serving a life sentence. (Simels also defended former Jets Ken O'Brien and Marc Gastineau to satisfaction in their respective assault charges in the '80s; O'Brien's stemmed from a Studio 54 brawl, Gastineau's from a domestic incident.)

Retired FBI agent Mark Johnston—who helped build cases against Mickens, Nichols, McGriff, and several of their associates—remembers Simels from those cases as a defense attorney who could come off as "crass and offensive," was capable of offending judge and jury alike, and would fight tooth and nail to contest even the most minor procedural issue. "Even though a lot of this is a show," says Johnston, "the defendant might think, 'Hey, this guy is really willing to be a rebel and fight for me', but all he's doing is ticking everybody off, and, in the long run, that is not going to serve you well."

In fact, court documents show that the presiding judge in the Mickens trial eventually recused himself from the case "due to the acrimonious relationship" that developed between him and Simels during the trial, and eventually recommended Simels for censure. The basis for disciplinary action was detailed in a 2005 memorandum denying Mickens's motion for a reduced sentence. Eastern District Judge Joanna Seybert concluded that Simels did not relay an offer of a plea deal to Mickens so that he could continue to collect legal fees. The judge wrote that Simels helped Mickens execute a power of attorney in the name of one of Mickens's aliases, so that Mickens's brother could access two safety deposit boxes that were said to be stocked with ill-gotten money. That, coupled with subsequent trips by Simels to Jackson, Mississippi, where the safety-deposit boxes were located, wrote Seybert, "raise the specter that Simels may have been willing to compromise his ethical obligations in an effort to be paid."

How much the word "ethics" will be bandied about in Gleeson's courtroom is anybody's guess. As the April trial date in the case against Bob Simels approached, the prosecutors' net seemed to have tightened around him. The government unsealed a new indictment against Simels based on evidence found amid materials confiscated from Simels's law office, which included "illegal electronic eavesdropping equipment, approximately $2,500 in cash, jewelry, a loaded firearm, and computers." The prosecution clearly felt confident enough in the new evidence to risk the likely postponement of the trial, which is now scheduled for July—at which time Bob Simels's tactics as a lawyer will get more public notice than he ever dreamed of.

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